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The Chinese flights came a day after the US secretary of state warned Beijing that Washington was committed to the defense of the democratic, self-governed island, which China considers part of its sovereign territory.
The 25 planes dispatched by China's People's Liberation Army (PLA) forces included 14 J-16 fighter jets, four J-10 fighter jets, four H-6K bombers, two anti-submarine warfare planes and an airborne early warning and control plane, according to Taiwan's Defense Ministry.
Taiwan responded by scrambling combat aircraft, alerting missile defense systems and issuing radio warnings to the Chinese planes that they had entered the southwestern corner of the island's self-declared air defense identification zone (ADIZ), a ministry statement said.
A graphic supplied by the ministry showed flight tracks for the Chinese aircraft coming from and returning toward the Chinese mainland, making 180-degree turns between the main Taiwanese island and Pratas Island, southeast of Hong Kong.
Taiwan began posting regular updates on PLA flights near the island last September. Before Monday, the largest number of Chinese warplanes to enter Taiwan's ADIZ was 20 jets on March 26.
The US Federal Aviation Administration defines an ADIZ as "a designated area of airspace over land or water within which a country requires the immediate and positive identification, location, and air traffic control of aircraft in the interest of the country's national security."
Chinese planes have been making almost daily incursions into Taiwan's ADIZ in recent weeks, as tensions heat up between Beijing and Taipei's main supporter, the United States.
Beijing claims Taiwan as its territory, even though the democratic island of almost 24 million people has been governed separately for more than seven decades.
Chinese President Xi Jinping has vowed that Beijing will never allow Taiwan to become formally independent and has refused to rule out the use of force, if necessary, to unify the island with the mainland.
Analysts said the exercises were a warning to Taipei and Washington that Beijing would not brook any moves for Taiwanese independence and was prepared to act militarily to prevent that from happening.
US Secretary of State Antony Blinken on Sunday said Washington was standing by a commitment to defend Taiwan.
"What is a real concern to us is increasingly aggressive actions by the government in Beijing directed at Taiwan," Blinken said on NBC's "Meet the Press."
"We have a serious commitment to Taiwan being able to defend itself. We have a serious commitment to peace and security in the Western Pacific. And in that context, it would be a serious mistake for anyone to try to change that status quo by force," Blinken said.
Monday's Chinese flights into Taiwan's ADIZ continue a pattern, said Bonnie Glaser, director of the China Power Project at the Center for Strategic and International Studies.
"Every time the United States takes a position regarding Taiwan which China doesn't like or if Taiwan does something that they don't like, it usually ratchets up the activity inside Taiwan's air defense identification zone, and sometimes around some of the islands that Taiwan occupies in the South China Sea," Glaser said.
China is quickly amassing weapons and systems to militarily overwhelm the island, the leaders said.
"My opinion is this problem is much closer to us than most think," Adm. John Aquilino, the admiral chosen to be the next commander of US forces in the Pacific, warned last month in a hearing before the Senate Armed Services Committee.
China considers establishing full control over Taiwan to be its "number one priority," added Aquilino.
The current head of the command, Adm. Philip Davidson, told a hearing earlier this month that China could be prepared to take Taiwan by force within the next six years.
CNN's Angus Watson and CNN's Beijing bureau contributed to this report.